Mistress J's Stepmother!

Pulling her tongue out of my rear Jackie sounded out of breath giving my ass a slap telling me that now was the time. Kneeling behind me Jackie gave my ass another slap giggling telling me her favorite thing to do is deflowering young boys with her strapon but today was going to be extra special since I was her daughter's boyfriend. Jackie told me to hold still and get ready for the ride of my life. Rubbing the head of the dildo up and down my crack Jackie could tell I was a little tense so she began talking to me in her soft sexy seductive voice convince me to relax my anal muscles permitting her to enter me with the head of her cock. The whole time she was talking Jackie was delicately wiggling the head around and around my anus telling me to push as if I was expelling something. As soon as I started pushing this enabled her to push the head of the dildo inside my anus past my delicate unstretched sphincter muscle giving me the surprise of my life as my bowels were filled with a burning pain followed by the immediate desire to expel the dildo. Listening to my heavy breathing knowing that I was a little tense Jackie promised me that that it already was too late to pull out so I may as well relax and allow her to take my virginity.

Telling me to grab my cock with my right hand and start stroking which will help keep my mind off my asshole warning me not to come too soon because her cock never goes soft. I could feel Jackie slowly rotating the dildo like a drill forcing the head in deeper. I actually started getting pleasure when they head pressed against my prostate gland causing my cock to begin expelling pre-come. With the dildo inside at least 3in. Jackie skillfully started pushing and pulling the head of the dildo back and forth across my prostate gland making me begin to squirm as this new form of pleasure started rising up within me. I started stroking my cock in rhythm with the dildo forgetting all about the painful anal entry which was still on fire. Jackie kept on urging me to keep stroking my cock talking to me in her sexy voice to stay relaxed so that she can finish deflowering me. I finally got the message and I continued straining which relaxed my anal muscles just enough for her to keep pushing. When she had the dildo 6in. inside Jackie started fucking me a little faster and harder forcibly inching the dildo farther and farther into me. I could feel the outside of my anus getting stretched to the max as my loose skin of my outer anus was pushed and pulled along her shaft. I was sure she loved the site of watching her dildo taking my cherry.

Stopping momentarily with the dildo still at the 6in. mark Jackie leaned forward stuck her long nails into my shoulders and told me to take a deep breath and then release. I could feel her beginning to rotate her hips and as soon as I expelled the air from my lungs Jackie lunged her powerful hips forward driving the dildo all the way inside to the hilt. I could even feel the cold brass ring against my anus. My entire body felt like it was on impaled on a fence post. I opened my mouth and cried out thinking that the head of the dildo was going to jut out of my mouth. My entire being wanted to buck Jackie off of me and work lose of her dildo. Keeping her hips tightly fastened against me Jackie held on to my shoulders riding me like a stallion. Every part of my psychological being told me I was on the wrong end of the stick. The stallion was supposed to be doing all the fucking. As I fought the losing battle all my homophobic thoughts came to mind. Bargaining with myself I admitted I was in the privacy of Jackie's bedroom getting taken by her artificial silicone cock. All she was sharing with me was to give me to understand of an alternative lifestyle that included a different way to view the world including a different kind of pleasure. I was also a captive in a mistress bedroom under her magical spells under her will. To Jackie pleasing the goddess meant subjugating men under her. Thinking like this comforted me some but I was still forcibly impaled.

As soon as I stopped fighting and settled down taking a deep breaths and slowly gasping for air I turned around and admitted to Jackie it was too late she had taken my virginity and I wanted her to fuck me. Settling into the pillows I put my head down and arched my bottom upwards giving her better access to my asshole. Grinding the dildo around and around inside of me Jackie swatted my cheeks several times crying out loud glorifying the goddess that another boy has lost his virginity. Leaning forward Jackie recited a short prayer dedicating me to the goddess.

(I give you this boy who has willfully allowed me to take his virginity honoring the goddess. Free him from his homophobic fears and open up his anus to new pleasures that I'm about to give him. My dildo which has opened up his asshole opened the door for me to give him male partners who also worship the goddess openly experimenting with his new sexuality. May he free from disease and only healthy partners couple with him. Free him from the fears of oral copulation as I teach him how to be an excellent cocksucker. I take charge of this slave and all of his sexual teachings making sure that he is properly disciplined in obedience to the laws of the goddess.)

With the dildo slowly pulling out of my asshole I contemplated this lifestyle that she dedicated me to the goddess but I told myself that I just had to trust Jackie and new sexual possibilities will come to pass. Talking to me in her sexy voice Jackie told me to keep my legs open, relax and just enjoy the ride. I couldn't believe how good she used her hips twisting and grinding the dildo in and out of my asshole plunging in full depth each time. My entire body rocked back and forth to the fucking. Instead of crying out like I did at first I started moaning joyfully concentrating on the head of the dildo sliding back and forth across my prostate. My cock was rock hard and spewing fluids each time she pressed forward. For the first time in my life I realized that getting fucked by someone with a cock I really didn't have to do any work but just enjoy my goddess treating me to anal intercourse. Soon Jackie had me by my ponytail pulling my head backwards and fucking me at the same time enjoying another boy she has successfully violated and taken his cherry. I found out later on that Jackie had a wooden dildo with notches for every boy and girl she has stripped of their cherries.

Sliding the dildo faster and faster Jackie was getting quite turned on when I heard her passionate cries I started masturbating faster and actually came with her as she screamed in passion I started squirting my sperm wastefully all over my chest and belly giving myself a sperm shower. To my amazement Jackie continued fucking me still enjoying her orgasm. Each time the head of the dildo slid past my prostate I drooled more come from my cock all over my hand. I remembered Jackie telling me that her cock never goes soft like mine which was already going limp after spewing my come all over myself. I then realized that Jackie was multi-orgasmic and definitely was not going to stop with her first orgasm of the night. I could tell my asshole was a little sore so I started bargaining with Jackie asking her for break. Slapping me harshly on the ass several times telling me never to question a dominant woman telling me to just shut up and keep stroking my cock forcibly pushing my head back down on the bed telling me they keep my butt up so she could slide in and out of my ass easier. Jackie continued thrusting deeply pounding her thighs against my backside turning both of us into a sweaty duo.

Grabbing my sticky half limp cock I started stroking again and to my surprise with the dildo constantly sliding in my asshole I was actually getting excited again. I got another surprise when I felt the dildo begin to vibrate. I looked around to ask Jackie what was happening and she started giggling knowing that I just felt the vibrator turn on. Giving me several more playful slaps on the ass which still made me jump she told me that the vibrator will help both of us on our next orgasm telling me to just shut my mouth and enjoy butt-boy. The vibrations definitely took my mind off my painfully stretched anus sending shivers up my spine. I could even feel my balls beginning to vibrate which seemed to help me gain back my erection. I started thinking about when I fucked Judi yesterday she complained about my premature ejaculation forcing me to go down on her because I couldn't continue screwing her to orgasm. I can still see her pussy full of my come she forced me to suck out. Now I was finding out firsthand the power of a strapon because Jackie could screw me all night long as long as she had the energy because her larger silicone cock would never go soft.

The vibrations we're finally getting to me and I became more relaxed accepting my place beneath my Mistress. I began moving with her instead of against her slowly rotating my hips rhythmically to her thrusts. Jackie even complemented me finally giving in to her and enjoying the moment telling me that this is what it is going to be like from here on out. My mind started going crazy because I really didn't understand what she just said. Sensing my confusion which made me tighten my grip with my anal muscles on the shaft of the dildo making it harder for Jackie to continue thrusting forcing her to push the dildo all the way into me to the hilt, Jackie slowly rotating her hips and began explaining. Grabbing my ponytail pulling my head back so that I could see her face talking to me in a stern voice Jackie told me that taking my virginity tonight is just the beginning of my training promising me she and her daughter Judi will be involved in every nasty new thing that will happen to me. I'm going to be introduced to sexual sensations I never thought of before. Finally telling me the most important thing is just to relax and enjoy this moment getting fucked by a beautiful experienced dominant woman.

Giving me several more stinging slaps Jackie told me to settle down and get comfortable because she was going to ride my devirginized ass all the way home. Pulling her artificial cock almost completely out Jackie turned off the vibrator telling us it was time for more lube. I could feel Jackie spilling lubricant down my butt crack and all over the dildo sliding it in and out several times and she continued pouring the cold gooey substance making my sore asshole easier to continue fucking. Jackie told me that she was taking good care of her daughter's buttboy because she wanted my ass to last for a long time. Sliding the dildo back inside my ass she turned vibrator back on. I started playing with my cock again which was almost fully erect. This time with all the negative feelings and pain removed I actually was beginning to enjoy getting fucked by this beautiful dominant woman. I started crying out her name exclaiming; "Oh Jackie, oh Jackie" over and over again. And then I started crying "oh god" and Jackie corrected me with a sharp slap on the ass telling me to cry out "Oh Goddess" instead because this is what losing my virginity was all about pleasing the goddess.

Suddenly as the end of the dildo contacted my stretched anus it started giving me an electric shock making me jump each time the dildo bottomed out. Giving me another slap on the ass Jackie started giggling telling me not to be shocked that she can still add a little bit of pain to my anal seduction. Each shock was so intense it seemed to make sparks fly out the end of my cock causing it to become rock hard. I found out later on that all of the nerve cells in my asshole and my cock are interconnected which was why the shocks were enabling my erection. I could hear Jackie squirming and crying out each time I was shocked telling me she was feeling the same thing through pussy lips. I told myself that this woman was one tough lady actually enjoying the vibrations and shocks along with myself. All this extra stimulation sent me over the top first. Squeezing the head of my cock desperately trying not to come I felt Jackie's hand forcefully push mine away grabbing me by the balls pulling them away from my body just in time to save me from another premature ejaculation. Keeping her grip on my balls Jackie continued fucking, vibrating, and shocking me driving both of us to another powerful orgasm.

When Jackie started coming she pushed the dildo all the way inside my asshole which made it give both of us a continuous shock. Releasing my balls I started coming into the palm of her hand ejaculating so much my semen I thought I completely emptied my balls. Both of us were shaking from the vibrations and constant shock. Finally Jackie came down from her orgasm switching the dildo off. Pulling my head back by my ponytail Jackie took her handful of come rubbing it all over my mouth forcing it open with her fingers and pushing all of it inside demanding that I swallow. I gulped down another forced load as she treated me just like her daughter. Telling me I was a good boy when she finally saw me swallowing adding that I need to get used to the taste because there was going to be a lot more flooding my throat from now on. Jackie's own daughter Judi was the first one to force me to eat my own come right out of her pussy after fucking her but I was still not used to the thought of swallowing semen even if it was my own. It still seemed quite nasty an unnatural yet being forced to do something dirty was actually a turn on for me. Licking my lips free of come I told Jackie that was the hottest orgasm I ever had. Slapping my ass Jackie promised me she could do that for me all the time.

Slowly sliding the dildo out of my ass Jackie told me she was going to make a dildo change because now since my asshole was so relaxed I will be able to accommodate an even larger one. I watched Jackie walk over to her bureau where the housemaid had placed some wine pouring of us both a glass. My asshole was still tingling from the fucking and shocking but I obediently remained butt up over the pillows knowing I was about to be fucked once again. I was so overcome by lustful thoughts my hips were already moving as if I was getting fucked by a phantom cock. Watching me Jacking told me not to worry my body is now grieving for more cock which she will satisfy soon. I found out later on that Jackie had used an anal lube on my asshole to relieve pain and make it relax more which will enable her to use the bigger dildo. Before Jackie returned with the two wineglasses I watched her remove the sticky dildo from the brass ring wrapping several wipes around it for washing later on. She opened a drawer and pulled out a black 10in.long dildo that was at least 2in.wide in diameter. With a big smile on her face she slipped it into her harness stroking and pointing it directly at me telling me once I'm fucked by this cock Goddess Jackie will know she has taking your full anal virginity.

I was a little shaken from getting fucked twice already yet my asshole was twitching for more. I couldn't figure out why I was so sexually turned on. I found out later on that Jackie had slipped me something which helped me relax making me desire more sex along with the magic blue erection pill. The magic potion was mixed with the enema she gave me which was the reason why she forced me to hold it for so long so the drugs could get into my system. Jackie brought me a glass of wine and sat down in front of me. As we sipped the expensive pinot noir wine Jackie told me I was the hottest boy she ever had the pleasure of taking my cherry and was definitely looking forward to fucking me again as soon as we finished our wine. Taking my hand and she placed it on her cock telling me to stroke it. As soon as I started rubbing the huge shaft I told her it was quite large. Jackie assured me that is surely was but with her in the saddle I had nothing to worry about. Finishing her glass of wine Jackie took my glass away from me setting it on a nearby table. Kneeling in front of me she started rubbing my cheeks with the head of the dildo telling me how much she enjoyed fucking me and how submissive I was at allowing her take me so easily. Jackie started telling me that this new dildo was crafted from her housemaid Myra boyfriend's cock confessing that she had the real thing pushed into own asshole just last week and maybe somehow that what happen to me. In a soft seductive voice she began rubbing my lips with the head of the dildo pulling my chin down telling me to open my mouth wide.

As soon as she had my mouth open she pushed the dildo inside a good 6ins. until I was gagging. Pulling back but keeping the dildo in my mouth she started giggling telling me now I know what it feels like for a man to force a huge cock into a woman's mouth undeservingly adding that when she is done training me I'm going to be able to swallow the whole thing without choking. Having already sucked and swallowed her smaller dildo this one was really going to be a challenge to swallow let alone taking it all the way into my asshole. The head of the dildo was definitely a lot larger than the last one which was going to take Jackie a lot longer to push it into my tight rear. I was actually getting turned on being forced face fucked with Jackie holding my ears pulling my mouth up and down the shaft with the head of the cock bouncing against my uvula. Fucking my face until my mouth had saliva drooling down my cheeks and chest until my throat was sore from forced cock sucking Jackie pulled the dildo from my mouth and started slapping my face back and forth with her cock until I saw stars telling me that even though she knew I didn't enjoy this experience there would be a lot more time for cock sucking in the near future.

Taking a drink of my wine she handed the glass to me ordering me drink it all which I quickly swallowed down. The wine actually had another magic potion which started making me horny again. I found out later on that Jackie was also taking a similar potion which helps ensure her to be multi-orgasmic all night long.

I could hear Jackie putting a rubber glove on her left hand and opening up a can of thick oily lube. With two greasy fingers Jackie started pushing them deep into my still dilated asshole massaging and stretching it until she got three fingers inside. Going slow and taking her time stretching and lubricating as she went Jackie was able to get all four fingers and part of her thumb stretching my anus to the max. I was already crying out to the goddess getting very uncomfortable and not knowing what was going to be next. Jackie kept reassuring me that she was in total control and would never let anything happen to my precious asshole because she has lots of plans for me. Jackie continued fingering me making sure that I was well lubricated. Finally she removed her fingers and snapped off the glove. I could feel the bulbous head of the dildo pushing against my anus like a large battering ram. Speaking softly to me ordering me to push just like I did for the other dildo with a little bit of straining she was able to get the huge head inside. As soon as the head popped past my sphincter muscle the sensation made me feel like I was getting ripped apart I started crying out and bucking once again.

Not wanting to cause too much pain Jackie pulled free and applied more lubricant to both my asshole and the huge black dildo. Wiggling the head Jackie pushed her battering ram back inside for another painful rear entry causing me to cry out squealing like a baby. This time there was no mercy as I felt a steady pressure from Jackie's hips slowly driving the dildo inside. Rotating her hips like a drill using the same technique she used last time Jackie was able to get a good 7ins. inside quite fast. I could feel my insides spasming around the huge dildo and my anal muscles were clamping out of control trying desperately to expel the huge foreign object. Mistress was too skilled for this because she was determined to skewer me completely on all 10 inches. Ignoring my cries and pleads for her to pull free, Jackie started fucking me nice and slow easing the dildo into me farther and farther every time she pushed inside. Slapping my butt real hard ordering me to stay relaxed and focus on pushing back it only took her about five minutes and she had the entire dildo buried in my ass. Celebrating she began whipping my bare behind with both hands at the same time. She was spanking me so hard I was fucking myself by pulling away trying to get away from the spanking only to have her drive the dildo back inside with her powerful hips.